DE719366C - Process for the preparation of salts of the N-acyl derivatives of p-aminophenylstibic acid - Google Patents
Process for the preparation of salts of the N-acyl derivatives of p-aminophenylstibic acidInfo
- Publication number
- DE719366C DE719366C DES128190D DES0128190D DE719366C DE 719366 C DE719366 C DE 719366C DE S128190 D DES128190 D DE S128190D DE S0128190 D DES0128190 D DE S0128190D DE 719366 C DE719366 C DE 719366C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- salts
- aminophenylstibic
- acyl derivatives
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/90—Antimony compounds
- C07F9/92—Aromatic compounds
Description
Verfahren zur Herstellung von Salzen der N-Acylderivate der p-Aminophenylstibinsäure Im Hauptpatent d9365 ist gezeigt, daß die p-Aminophenylstibinsäure mit Glucamin und dessen Derivaten beständige Salze liefert, die eine recht geringe Giftigkeit und eine therapeutische Wirksamkeit besitzen.Process for the preparation of salts of the N-acyl derivatives of p-aminophenylstibic acid In the main patent d9365 it is shown that p-aminophenylstibic acid with glucamine and its derivatives give stable salts which are very low in toxicity and have therapeutic efficacy.
Es ist nun weiter gefunden worden, daß auch die N Acylderivate der p-Aminophenylstibinsäure mit den Aminen der Polyalkohole und insbesondere mit Glucamin und dessen Derivaten sehr beständige lösliche Salze geben, die bei verminderter Giftigkeit eine viel größere therapeutische Wirksamkeit, z. B. auf die Nagana der Maus, ausüben als die entsprechenden bekannten Salze.It has now been found that the N acyl derivatives of p-aminophenylstibic acid with the amines of the polyalcohols and especially with glucamine and its derivatives give very stable soluble salts which, when reduced Toxicity a much greater therapeutic efficacy, e.g. B. on the Nagana of Mouse, exercise known as the corresponding salts.
Die Herstellung dieser Salze erfolgt in gleicher Weise wie im Hauptpatent angegeben: Im nachstehenden sind Beispiele für die Herstellung der N-Methylglucamin- oder der Glucaminsalze von N - Acylderivaten der p-Aminophenylstibinsäure angegeben.These salts are produced in the same way as in the main patent indicated: The following are examples of the preparation of the N-methylglucamine or the glucamine salts of N - acyl derivatives of p-aminophenylstibic acid.
Beispiele i. Man löst bei 55° auf dem Wasserbad i 5 g der Harnstoffverbindung der p-Aminophenylstibinsäure und i o g N-Methylglucamin (oder 'die entsprechende Menge Glucamin) in q.5 ccm Wasser, filtriert und gießt die erhaltene Lösung in die i ofache Menge ihres Volumens an absolutem Äthylalkohol, quetscht aus, wäscht mit absolutem Alkohol und trocknet im Vakuum.Examples i. 5 g of the urea compound are dissolved in a water bath at 55 ° of p-aminophenylstibic acid and 10 g of N-methylglucamine (or the corresponding Amount of glucamine) in q.5 ccm of water, filtered and poured the resulting solution into the i ofache amount of their volume of absolute ethyl alcohol, squeezes out, washes with absolute alcohol and dries in a vacuum.
Die als Ausgangsstoff dienende Harnstoffverbindung kann wie folgt erhalten werden: g der noch feuchten, nach dem Verfahren von S c h m i d t (;Annalen der Chemie<; 19 22 [q.29], S. 145) frisch bereiteten p-Acetylaminophenylstibinsäure werden mit einer Lösung von i o g Glycerin, 2o ccm Methylalkohol und 125 ccm Wasser verdünnt und hierzu 3 g Natriumacetat sowie eine Menge Natronlauge gegeben, die zur Lösung der p-Acetylaminophenylstibinsäure gerade genügt.The urea compound serving as the starting material can be obtained as follows: g of the p-acetylaminophenylstibic acid, freshly prepared by the method of S c hmidt (; Annalen der Chemie <; 1 9 22 [q.29], p. 145)) are still moist a solution of 100 ml of glycerine, 20 cc of methyl alcohol and 125 cc of water and added 3 g of sodium acetate and an amount of sodium hydroxide solution which is just sufficient to dissolve p-acetylaminophenylstibic acid.
Der erhaltenen, auf + 3° abgekühlten Lösung wird alsdann langsam unterUmrühreneine Lösung von i g Phosgen in 5 ccm Essigsäure zugegeben. Hiernach fällt die Harnstoffverbindung der Diphenyl-q., q.'-distinbinsäure aus. Man schleudert ab und wäscht mit eiskaltem destilliertem Wasser.The resulting solution, cooled to + 3 °, is then slowly mixed with stirring A solution of 1 g of phosgene in 5 cc of acetic acid was added. The urea compound then falls of diphenyl-q., q .'-distinbic acid from. You spin off and wash with ice cold distilled water.
2. 15,3 g p -Acetylaminophenylstibinsäure werden in einer wäßrigen Lösung von 10,2 g Methy-lglucamin aufgelöst. Die filtrierte Lösung wird in einen großen iberschuß von Alkohol gegossen, der gebildete Niederschlag durch Filtrieren abgetrennt, mit Alkohol gewaschen und im Vakuum getrocknet. Man erhält so das p-acetylaminophenylstibinsaure Methylglucamin in Gestalt eines weißen, in Wasser sehr leicht löslichen Pulvers.2. 15.3 g of p -acetylaminophenylstibic acid are in an aqueous Dissolved solution of 10.2 g of methyl lglucamine. The filtered solution is in a Pour a large excess of alcohol and filter the precipitate separated off, washed with alcohol and dried in vacuo. This gives p-acetylaminophenylstibic acid Methylglucamine in the form of a white powder that is very easily soluble in water.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES128190D DE719366C (en) | 1937-04-01 | 1937-07-27 | Process for the preparation of salts of the N-acyl derivatives of p-aminophenylstibic acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE501232X | 1937-04-01 | ||
| DES128190D DE719366C (en) | 1937-04-01 | 1937-07-27 | Process for the preparation of salts of the N-acyl derivatives of p-aminophenylstibic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE719366C true DE719366C (en) | 1942-04-14 |
Family
ID=25944772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES128190D Expired DE719366C (en) | 1937-04-01 | 1937-07-27 | Process for the preparation of salts of the N-acyl derivatives of p-aminophenylstibic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE719366C (en) |
-
1937
- 1937-07-27 DE DES128190D patent/DE719366C/en not_active Expired
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